Take it from one of the few NBA players who has done it not once, but twice, winning a three-peat is no easy task.

Scottie Pippen, of course, teamed with Michael Jordan as the Bulls won titles in 1991-93, then again in 1996-98. As the Miami Heat enter the season as two-time defending champions, they’re aiming to become the first NBA team since the Lakers in 2002 to make it three in a row.

So it only seems appropriate that the Bulls will be the first to stand in the Heat’s way when the 2013-14 NBA regular season gets underway Tuesday in Miami.

“The difficulty comes down to your competition,” said Pippen. “Because of that, I think this will be a very challenging year for Miami.”

Pippen knows plenty about being challenged. Whether it was Patrick Ewing’s New York Knicks in the early ‘90s or Reggie Miller’s Indiana Pacers in the late ‘90s, Chicago faced its share of obstacles. At the same time, the dynasty Bulls only played in two Game 7 series during their six championship seasons and both were prior to the NBA Finals.

“We were challenged,” acknowledged Pippen. “And Miami has been challenged, last year in particular. Obviously the Bulls weren’t able to put up the fight in the playoffs they would have liked, but Indiana emerged and presented a very formidable challenge and San Antonio had the Finals won. The Spurs were very close to knocking them off and preventing a back-to-back. A lot of it comes down to getting healthy and staying healthy.”

"Now that he’s gone through the injury and he’s had to watch other teams win and celebrate, that’s something that as a player, you learn and it makes you dig down and work harder," said Pippen of Rose.

(Scott Cunningham/NBAE/Getty Images)

That’s one thing Jordan and Pippen’s Bulls were able to do, though Pippen dealt with severe back pain frequently towards the end of the team’s championship run.

“Miami is in a similar position to where we were during our first three-peat,” said Pippen. “We were young, we had core guys who had played together for a few seasons, and we rode it all the way to a third title. The Heat will face a lot of the same challenges we did. Everyone will be gunning for them, so it’s just a matter of what their competition will be able to do.”

Enter the Bulls, who have Derrick Rose back in a lineup that when healthy will include Jimmy Butler, Luol Deng, Joakim Noah and Carlos Boozer. Coupled with a formidable bench and Tom Thibodeau on the sidelines, Chicago again has championship aspirations. But the Bulls are hardly the only team in the Eastern Conference capable of knocking off the defending champions.

“I do see some teams, especially in the East, with Chicago, Indiana and Brooklyn who are certainly not going to roll over,” said Pippen. “These are teams who are familiar with Miami, so they have an idea of what it takes to defend the Heat and give them their best shot.”

“You’ve got to play through adversity,” Pippen continued. “You’re going to be challenged each and every night. Calls aren’t always going to go your way. So you’ve got to be able to play above all of that and not be distracted. Get your 12 or 13 guys in tune with what you’re trying to accomplish and play good basketball over a long stretch.”

Over the past three seasons, Chicago has proven it can beat Miami in the regular season with or without Rose. It’s the postseason where the Heat has had the upper hand, though the undermanned Bulls did score an upset win in Game 1 of their second round series in the 2013 playoffs.

“I think the Bulls have had success against the Heat because they’re not afraid of them,” said Pippen. “They believe they can beat them. We haven’t fared as well against them in the postseason because we haven’t been able to play our best basketball in the playoffs. We’ve lost some close games in recent years and those can often make the difference in a series. To me, the Bulls are capable as being just as dominant as Miami.”

While staying healthy is an obvious key to Chicago’s success, Pippen stressed that the team can’t – and under Thibodeau certainly won’t – forget about the other contenders in the East.

“Indiana can’t be overlooked,” said Pippen. “Whether it is Chicago or Miami, someone is going to have to get past them. But clearly the most important thing for the Bulls is to be healthy and at full strength. That’s going to determine what we can do in the postseason. If we’re healthy against Miami, I’ve got no doubt in my mind that we can beat them.”

Pippen, who works as the team’s Special Advisor to the President & COO, has been a regular at team practices since the start of training camp. Like everyone else, he’s excited for the season to get started.

“I think it’s definitely the best team we’ve put on the floor in a long time when you factor in the talent and maturity of the players,” Pippen stated. “Derrick was great two years ago; he was the MVP of the league. But was he ready to be a champion? I’m not going to say he wasn’t, but I think he would agree that it’s been a learning curve. Now that he’s gone through the injury and he’s had to watch other teams win and celebrate, that’s something that as a player, you learn and it makes you dig down and work harder.

“You do what you’ve got to do to get to the top,” Pippen added. “The Bulls are at that stage now. Enough has been thrown at our team and at our players. They’re ready to change the landscape of how they’re viewed.”